EP 3369724 B1 20210106 - PROCESS FOR THE PREPARATION OF IOPAMIDOL
Title (en)
PROCESS FOR THE PREPARATION OF IOPAMIDOL
Title (de)
VERFAHREN ZUR HERSTELLUNG VON IOPAMIDOL
Title (fr)
PROCÉDÉ DE PRÉPARATION D'IOPAMIDOL
Publication
Application
Priority
- EP 13191551 A 20131105
- EP 14796024 A 20141104
- EP 2014073692 W 20141104
Abstract (en)
[origin: WO2015067601A1] The present invention discloses a process for the preparation of Iopamidol of formula (II) and comprising the following steps: a) reacting the Compound (I) wherein X is OR2 or R3, and wherein R2 and R3 are a Ci-C6 linear or branched alkyl, C3-C6 cycloalkyl, C6 aryl, optionally substituted with a group selected from the group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, t-butyl and phenyl, with the acylating agent (S)-2-(acetyloxy)propanoyl chloride in a reaction medium to provide the acetyloxy derivative of Compound (I); b) hydrolyzing the intermediate from step a) with an aqueous solution at a pH comprised from 0 to 7, by adding water or a diluted alkaline solution such as sodium hydroxide or potassium hydroxide, freeing the hydroxyls from the boron-containing protective groups, obtaining the N-(S)-2-(acetyloxy)propanoyl derivative of Compound (II); c) alkaline hydrolysis to restore the (S)-2-(hydroxy)propanoyl group and to obtain lopamidol (II) and optional recovery of the boron derivative from the solution obtained in step b). The boron-containing protective group is versatile, efficient and recyclable. A one-pot synthesis, without intermediate isolation is provided, leading to a decreasing of recovered and recycled solvents and a significant increasing in the yield, representing a significant advantage in terms of cost-effectiveness of the entire process and environmental awareness.
IPC 8 full level
C07C 231/02 (2006.01); C07F 5/02 (2006.01); C07F 5/04 (2006.01)
CPC (source: EP IL KR RU US)
C07C 201/12 (2013.01 - IL RU US); C07C 227/04 (2013.01 - IL RU US); C07C 231/02 (2013.01 - EP IL KR RU US); C07C 231/12 (2013.01 - IL RU US); C07C 231/14 (2013.01 - IL RU US); C07C 237/06 (2013.01 - IL KR); C07C 237/46 (2013.01 - IL US); C07F 5/025 (2013.01 - IL RU US); C07F 5/04 (2013.01 - EP IL RU US); C07F 5/05 (2013.01 - EP IL KR RU US); Y02P 20/55 (2015.11 - EP KR US); Y02P 20/582 (2015.11 - EP KR US)
C-Set (source: EP US)
Designated contracting state (EPC)
AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR
DOCDB simple family (publication)
WO 2015067601 A1 20150514; AU 2014345727 A1 20160512; AU 2014345727 B2 20180705; BR 112016010223 A2 20180502; BR 112016010223 B1 20210525; CA 2927706 A1 20150514; CA 2927706 C 20180529; CA 3001399 A1 20150514; CA 3001399 C 20200630; CN 105705483 A 20160622; CN 105705483 B 20180904; DK 3066071 T3 20180730; DK 3369724 T3 20210329; EP 3066071 A1 20160914; EP 3066071 B1 20180418; EP 3369724 A1 20180905; EP 3369724 B1 20210106; ES 2674279 T3 20180628; ES 2862349 T3 20211007; HR P20181122 T1 20180921; HR P20210324 T1 20210402; HU E039440 T2 20181228; HU E053751 T2 20210728; IL 245457 A0 20160630; IL 245457 B 20200730; JP 2016539181 A 20161215; JP 6454351 B2 20190116; KR 102265049 B1 20210616; KR 102382351 B1 20220404; KR 20160081965 A 20160708; KR 20210072832 A 20210617; LT 3066071 T 20180910; LT 3369724 T 20210225; MX 2016005829 A 20170310; MX 2020010367 A 20210303; PL 3066071 T3 20180928; PL 3369724 T3 20210614; PT 3066071 T 20180625; PT 3369724 T 20210210; RU 2016122022 A 20171211; RU 2657238 C2 20180609; SI 3066071 T1 20180831; SI 3369724 T1 20210430; TR 201808527 T4 20180723; US 10377700 B2 20190813; US 2016237026 A1 20160818; US 2019071392 A1 20190307; US 2019077745 A1 20190314; US 9950991 B2 20180424; ZA 201602970 B 20170726
DOCDB simple family (application)
EP 2014073692 W 20141104; AU 2014345727 A 20141104; BR 112016010223 A 20141104; CA 2927706 A 20141104; CA 3001399 A 20141104; CN 201480060539 A 20141104; DK 14796024 T 20141104; DK 18162482 T 20141104; EP 14796024 A 20141104; EP 18162482 A 20141104; ES 14796024 T 20141104; ES 18162482 T 20141104; HR P20181122 T 20180716; HR P20210324 T 20210225; HU E14796024 A 20141104; HU E18162482 A 20141104; IL 24545716 A 20160503; JP 2016551022 A 20141104; KR 20167014721 A 20141104; KR 20217017633 A 20141104; LT 14796024 T 20141104; LT 18162482 T 20141104; MX 2016005829 A 20141104; MX 2020010367 A 20141104; PL 14796024 T 20141104; PL 18162482 T 20141104; PT 14796024 T 20141104; PT 18162482 T 20141104; RU 2016122022 A 20141104; SI 201430793 T 20141104; SI 201431776 T 20141104; TR 201808527 T 20141104; US 201415033737 A 20141104; US 201815912772 A 20180306; US 201816052695 A 20180802; ZA 201602970 A 20160504